Carbon Dioxide → 3,5-Dichloropyrazine-2-carboxylic acid

HRID 1007752Notes

Reaction equation

HRID 1007752 reaction equation
CC1(C)CCCC(C)(C)N1.C([Li])CCC.[Cl:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19]([Cl:23])[N:18]=1.[C:24](=[O:26])=[O:25].Cl>C1COCC1>[Cl:16][C:17]1[C:22]([C:24]([OH:26])=[O:25])=[N:21][CH:20]=[C:19]([Cl:23])[N:18]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 130352,2,6,6-TetramethylpiperidineHCID 785042,6-DichloropyrazineHCID 178418339Butyllithium

Product 1

HCID 226655363,5-Dichloropyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a THF solution of 2,2,6,6-tetramethylpiperidine was added n-butyllithium under ice cooling and was further added a THF solution of 2,6-dichloropyrazine at −78° C. After 30 minutes of stirring, dry ice was added to the reaction mixture and, after 30 minutes of stirring, 1 M hydrochloric acid was added thereto. Thereafter, purification in the usual way afforded 3,5-dichloropyrazine-2-carboxylic acid (pale yellow solid). FAB-MS: 191 (M−H)−.

Workup

  1. stirringof stirring
  2. customThereafter, purification in the usual way

Sources & evidence

ORD record
ord-ef85a469255e4bf281f669530eb456b0
Source dataset
uspto-grants-2004_09
Patent number
US06797706B1

Reaction notes

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